The best 'Will & Grace' guest stars of all time

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September 29, 2017

Over the course of eight seasons, Will & Grace showcased one incredible friendship and countless LOL-worthy moments. The hilarious series also attracted a lengthy list of celebrity fans and guest stars. From pop stars’ one-off appearances to Emmy-nominated turns by Hollywood legends, everyone wanted to join in on Will, Grace, Jack and Karen's shenanigans.

With Will and Grace returning to the small screen this fall, we couldn’t help but think back to a few of the show’s funniest celebrity cameos (think Madonna, Cher and Matt Damon).

Click through to see which episodes we think are worth revisiting. We can’t wait to see who will join this list next time we see Will, Grace and the gang.

Cher

One of Jack’s dreams came true when he had the chance to meet Cher during a surprise cameo in 2000. The problem was that he didn’t even realize it, and thought her impersonation of the “If I Could Turn Back Time” singer could use some improvement. Later, during season four, Cher reunited with Jack when she turned up in one of his dreams and encouraged him to pursue acting.

Debbie Reynolds

Madonna

Karen was newly divorced when she met the “Material Girl” as Liz, her potentially perfect roommate. The pair are completely in step during the 2003 episode until they discover they also have the same taste in men, which results in a hilarious slanging match.

Over the course of eight seasons, “we had a lot of other famous movie-star type of people but the pop stars were really interesting,” Megan noted recently. “Madonna was very cool.”

Ellen DeGeneres

It came as no surprise that Ellen counts the 2001 episode in which she plays Sister Louise as her favourite. Years after she filmed her stint on Will & Grace, the comedienne had the four leads on her daytime talk show, where Debra said she’d love to have Ellen back on set. She told the host: ”We need to make that nun recurring.”

Harry Connick Jr.

Fans went crazy for Grace Adler’s on-off love interest Leo, played by handsome singer-songwriter Harry, who would go on to become actress Debra Messing’s TV husband. Woody Harrelson was another on-screen beau.

Elton John

A 2002 episode featured the GRAMMY-winning legend as himself. In an unexpected run-in with Will, the superstar reveals he’s the head of the “gay mafia.” Over the years, other singers who played themselves on the laugh-out-loud series included Jennifer Lopez and Janet Jackson.

Glenn Close

When Will Truman (Canada’s Eric McCormack) wins a photoshoot with famous celebrity photographer Fannie Lieber (Glenn Close) at a silent auction, it means he’ll also appear in her new coffee table book. Grace is a huge fan of Fannie’s work, so he takes her along. Fannie is so enamoured with the best friends that she ends up kissing them both!

Matt Damon

Mere months before we first saw him as an action hero in the The Bourne Identity (2002), Matt appeared in the episode “A Chorus Lie” as a singer who vies with Jack for a solo spot in the gay men’s chorus. When Jack suspects Owen is straight, he enlists Grace to seduce him and sabotage his chances.

Britney Spears

All eyes were on the “Toxic” singer when she joined Jack McFarland (Sean Hayes) as a co-host on his talk show in 2006. Britney showed off her comedic chops as Amber-Louise from Alabama, a straight-laced southern belle who shocks Jack when she reveals she’s not as demure as she seems.

Joan Collins

In 2000, Karen Walker (Megan Mullally) put her sleuthing skills to the test by helping Grace find out more about design guru Helena Barnes. Dynasty star Joan played the elegant interior designer who competed with Grace for a client.